Letter from Elizabeth Upshur Teackle to her sister Ann Upshur Eyre, undated. The date of this letter is either April or May of 1799 due to context. The letter mentions the long awaited return of the ship Delaware, captained by John E. Sword from Canton. It discusses the wedding of Sarah Corbin Cropper, as well as mentioning Mrs. Vear, Henrietta Teackle, John Teackle, Mrs. John Dennis, Col. Cropper, and Col. Savage.

Letter from Elizabeth Upshur Teackle to her sister at Ann Upshur Eyre, sharing family news from the family home of her Uncle Littleton Upshur's home Vaucluse on Hungars Creek. People mentioned in the letter include Aunt Ann Parker Upshur, Juliet Upshur, Elizabeth "Betsy" Snead, and Dr. Hugh Ker.

Letter from Elizabeth Upshur Teackle to her sister at Ann Upshur Eyre, sharing family news from the family home of her Uncle Littleton Upshur's home Vaucluse on Hungars Creek. She discusses her engagement to Littleton Dennis Teackle, which is still a secret at this time, and mentions people such as Henrietta Teackle, Elizabeth Bowdoin McCroskey, her cousin Juliet Upshur, Betsy Snead, Uncle Littleton Upshur, John Teackle, and the home Eyreville.

Letter from Elizabeth Upshur Teackle to her sister, Ann Eyre, written from Kegotank. She discusses the arrival of a fancy wig for Ann from Philadelphia which cost $26. She shares news of the death of Abel Upshur Teackle.

Letter from Elizabeth Upshur Teackle to Caleb Upshur.

Letter from Elizabeth Upshur Teackle to her sister, Ann Upshur Eyre. She asks her sister to come visit with their cousin John Custis Upshur because her husband is away. She talks about Miss Harwood, Molly Gilmor, William Gilmor, John Taylor, Mary Winder, and George Kendall.